A Dasey Night Out
by leanaplumz
Summary: Derek leads Casey on a night around Toronto. What's his endgame?


**This is my first Life With Derek fic. I'm a huge Dasey shipper and although I don't see it actually happening on the show... maybe in the movie?  
I live in Toronto, so I tried my best to make this as realistic as possible. This timeline of the evening is totally off... as there is no way that you can have a Hockey game, watch Dirty Dancing, go to dinner and STILL have time to go skating... but who knows? Maybe the game was at 9 am! That's why this is a futurefic AND AU! lol. It may also be OOC.**

**Enjoy.**

Derek Venturi skated off the rink and hurried into the locker room. He had just played his 100th game in the NHL for his dream team – The Toronto Maple Leafs. He'd scored twice and had three assists, yet through out the entire game he could not get the image of his girlfriend and soon to be fiancé – he hoped – out of his head. He had the entire proposal planned out, and after all they had been through to get this far, he was sure there was no way she could say no. They'd been dating since their senior year of high school, both went to university in Toronto, him at Ryerson and her at York University and now shared a small apartment just off Front Street and minutes from the Air Canada Centre; a building Derek loved but couldn't wait to escape from today.

Casey Macdonald sat in the stands of the Air Canada Centre watching her step brother play his 100th game. He was poetry in motion, unstoppable on – and off – the ice. In her opinion, Derek was the best thing to ever happen to the Maple Leafs and she couldn't have been more proud of him. She'd watched him totally mature over the past few years under what she thought was the influence of his girlfriend. They'd both attended university in Toronto and had grown to be close becoming each other's best friend and connection to home. Casey would never have fathomed that back in high school that she and Derek would be friends, but now… now she couldn't imagine her life without him. As the game ended, she watched Derek race off the ice barely pausing to nod to the opposing team. Just before he disappeared he glanced up at Casey, caught her eye and gave her his infamous smirk.

Derek quickly showered and changed into the shirt Casey said brought out the hazel flecks in his eyes. Suddenly Derek was consumed by a wave of nausea. He rushed to the nearest toilet and emptied his stomach of all its contents. He couldn't believe how nervous he was! Even more so than before his first NHL game!

Casey had been waiting outside the locker room to congratulate Derek and see if he was up for their regular after game coffee date, only he had been in there for over half an hour. Starting to get worried, Casey pounded on the door.

"Der-ek! What's taking you so long?"

"I'm coming… I just need to take care of something."

Derek washed his mouth out and grabbed his coat, not noticing the small velvet box that fell out of his coat.

"Hey Case. Been waiting long?" Derek asked in his cocky way.

"Only since you raced off the ice so fast, it looked like you were being chased by bees!"

"Well, I couldn't wait any longer to see you."

"Oh yeah? To do what?"

"This." Derek wrapped his arms around Casey's waist and pulled her to him.

"Der-ek!" Casey whispered as Derek kissed her neck and jaw line.

"I never want to stop hearing you say my name." Derek whispered into her ear. "Now c'mon. I've got a great night planned for us!"

"Huh?"

"We are going to go watch _Dirty Dancing _at the Canon Theatre then I'm taking you out to dinner up at the Restaurant 360 in the CN Tower."

"Wow, Derek… Why?"

"Must you always ruin my moments with questions?"

"Yes. Now why?"

"Because, dear Casey tonight is a special night."

"If I'm getting the Princess treatment, I'd better not argue!"

"Now why can't you be this sensible all the time?" Derek smirked.

"Der- ek!" Casey slapped his arm.

Derek led a shocked Casey out to a waiting limo and held her arm as she slid in.

"I can't wait to see Dirty Dancing! I've been hearing wonderful things about the new actress they have playing Baby!" Casey gushed.

"Oh yeah? What's her name?"

"Ashley Leggat. Hometown girl… Hamilton. Some people say I look like her."

"Really? Then she must be gorgeous!"

"Good move."

"Thank you."

The limo pulled to a stop in front of the theatre and Casey suddenly was overwhelmed with giddiness.

"I LOVE musicals!"

"I know," Derek smiled and put his hand on the small of her back, leading her through the crowd.

Through out the entire show, Derek couldn't help but stare at Casey as she sang along with the songs and mouthed the lines along with the characters. He even burst out laughing when she cheered after Johnny uttered, 'Nobody puts Baby in the corner.'

As they left the theatre, Casey slid her arms around Derek's waist snuggling as close to him as she could. Since it was a mild night, Derek decided that they would walk the few blocks to the restaurant so they could have a chance to talk.

"Why are you being so nice?"

"… Do you not want me to be? I could very easily switch over to Bad Boy Derek."

"Now, while I do love Bad Boy Derek, I'm just curious why tonight is so special."

"Because I'm with you, Case."

"That is the cheesiest thing I've ever heard come out of your mouth!"

"Is it now?"

"Yeah it is. AND you still have not answered my question."

"Can't a guy celebrate a career milestone with his beautiful girlfriend and not have an alternative motive?"

"If that guy is you, then no."

"That hurt, Case. Right here." Derek pouted thumping his chest.

"Aww… poor Der-Bear!" Casey laughed.

"Not funny! Your gonna pay for that!" Derek reached out and started tickling Casey until she started to run away laughing.

"This is my city! You can run but you can't hide!"

Despite the stares the couple got, Derek chased Casey all the way to the base of the CN Tower.

Flushed and grinning, Derek and Casey stopped to catch their breath in front of the Tower.

"Y'know the limo tailed us the whole way? I think I saw the driver laughing."

"Well, I have him for the whole night… and I think we'll need him after dinner," Derek laughed.

"I've never been up there."

"Seriously, Derek?"

"Yeah. Dad's afraid of heights and he was always the one to bring us to Toronto. Usually it was for the CNE or something."

"I used to work at The Ex!"

"Really when?"

"In Grade nine and ten… before mom married George and we moved to London."

"I learn something new about you every day, Space Case," Derek said affectionately.

"Ok, enough with the mushy gushy stuff. I'm hungry!" Casey grinned and grabbed a smirking Derek, pulling him inside.

Once in the elevators, Derek slipped his arms around Casey and rested his chin on the crown of her head. As the elevator ascended, Casey could feel Derek's grip slightly tighten on her.

"So George isn't the only one afraid of heights, huh?"

"Uh… I think Edwin may be too."

Laughing Casey turned around and looked him in the eyes, "Not who I meant."

Since they had the elevator to themselves, Casey gave Derek a reassuring kiss.

"Y'kno, if I didn't love you I would be petrified of you knowing all my secrets."

"Oh so you admit you're scared!"

"Only to you. And if that leaves this elevator… so help me Go-"

Casey silenced him with another kiss, this one a little more passionate. "I love you too. Your secrets are safe with me."

"I remember the first time you admitted it."

"Yeah, well I remember how scared you were when I figured _you _out! And the look on your face when Marti and Lizzie found us kissing in the backyard for the first time. And when we had to tell George and mom… and then the whole school, you were shaking in your boots. I almost thought you were ashamed of being with me."

"I would never be ashamed of you Case. I was scared outta my mind though. Despite whatever image I put forward in high school, what people thought really mattered to me. What you thought mattered."

"You never seemed to care when you were bringing around Blonde Bimbos."

"You do realize that I only dated blondes because they were as far from you as I could get, right?"

"Now that makes me feel better!"

"No, not like that. Casey, I fell in love with you the minute I met you at the wedding. Before I knew who you were and what you were about to become. We talked and laughed and all I saw was this beautiful, smart and witty girl who had literally blown me off my feet."

"Derek."

"No. Let me go on. I don't know why I've never explained this to you before. I only dated those girls, _all_ those girls because -"

The elevator doors opened without Derek or Casey noticing until a couple tapped Derek on the shoulder. Sheepishly smiling, the couple got off the elevator and walked to the restaurant.

"THIS IS SO COOL!"

"Derek? You're yelling, hun."

"I'm the king of the world!"

"Uhh… maybe just Toronto."

"Look! I can see our apartment!"

"You're acting like an over excited 2 year old!" Casey grinned.

"Well, I'm an overexcited 25 year old, who just got a new perspective on life!"

"Whoa! Venturi the philosopher!"

Derek's cell phone began to play Casey's voice leading D-Rock.

"Hello?"

"Mr. Venturi? Are you still planning on joining us for dinner?"

"Oh gosh! What time is it Chyr?"

"9:17. Your reservation was for 9:00. You know, if Mats didn't speak so fondly of you I wouldn't even bother with this."

"He's a good guy to have around. I'm on the Viewing deck with my date. We'll be there in a few."

"Ok, I'll have the table set up for when you arrive. Are you still planning to have a special evening?"

"You better believe it! I couldn't think of a better way to cap off tonight."

"Hurry Derek, my manager is lingering."

"Be right there."

He hung up and turned to face a confused Casey.

"Come m'love. Grub's a-waiting!"

"Oh, very romantic."

"I try." Derek grinned.

When Dasey entered the restaurant, Chyr showed them to their seats and with a wink at Derek mentioned their waiter over.

Casey was amazed at all the attention Derek got while they were eating dinner. No less than 4 blushing teenage girls came up to him for autographs and a small star gazed boy around Marti's age shyly approached him as he was heading to the washroom. Derek crouched down to eye level, and smiled at the boy talking away with him as if they were old friends. The boy's mother stood there with a love struck grin on her face, which Casey could help but laugh at.

When Derek came back to the table, Casey attempted to give him the same love struck gaze, but ended up laughing.

"What's so funny? Do I have sauce on my tie?"

"No, but you're going to make a great dad one day."

"Ok," Derek drew out. "Why?"

"I've seen you all these years with Marti. And just now with that kid… he's going to treasure the moment that 'The Great Derek Venturi' took time to talk to him."

"He's a cool kid. Reminded me of myself when I was his age. He's a hockey player, but scrawny. He's always benched. I told him that I was a skinny kid too until I started working out and practicing hard. Look where it got me! A great career and an even greater girlfriend!"

"You are such a charmer!" Casey grinned.

"You know how I do." Derek smirked.

"Never. Never again are you to say that!" Casey laughed.

"Why not? I'm cool."

"Of course. The coolest. AND the whitest."

"What does that have to do with anything?"

"I dunno. It just does."

"Anyway, are you done?"

"Yes… although I am feeling for some of that cheesecake."

"Coming right up!"

Derek walked over to the desert counter and ordered a slice of the chocolate cherry New York cheesecake that he knew Casey would melt over and discreetly reached into his pockets for the ring, only to find it missing.

"Crap!" Derek muttered as he searched frantically through all his pockets.

"Are you alright, sir?" A passing waiter asked.

"No!" Derek panicked. "I lost my engagement ring!"

"Er – I'm sorry, sir?"

"The ring! I was going to propose to my girlfriend tonight, and I've gone and lost the blasted ring! How do you lose a ring?"

"Maybe it fell out of your pocket, sir."

Derek thought back to the events which had unfolded during the night. He thought about the ride up the elevator, the chase around downtown Toronto, rushing out of the locker room to meet Cas-. He remembered the thud as he left the locker room… his ring falling as he put his coat on.

"Crap!"

Sheepishly, Derek picked up the slice of cheesecake and headed back to the table.

"Are you okay, D?"

"Hmm? Oh yeah. Fine."

"Yeah, no you're not. What happened?"

"Nothing for you to worry about. I just remembered something I'd forgotten."

Sceptically, Casey nodded and dug into her cake. "This is delicious!"

"Gimmie here!" Derek pulled the plate to him with as real a grin as he could muster. "That is good."

After they finished dinner, Derek contemplated going back to the arena to get the ring but decided against it. He didn't need a ring to let Casey know how much he loved her!

The couple climbed into their limo and headed towards Derek's final planned spot for the night – Nathan Philips Square. As they skated, Derek formulated a new plan to propose to Casey with out his ring. After dismissing all ideas, Derek decided to suck it up and dropped to one knee.

"DER-EK! Are you alright?"

Derek now kneeling in the middle of the rink took Casey's hand and gazed into her eyes.

"Derek what are you doing?"

"Casey. You know I love you. I'd do anything for you. I'm also not the best versed dude out there, but I want to make you happy. I want to spend the rest of my life making you happy. I'd had a whole night planned out, the show, dinner, skating… all leading up to this moment. However your klutzillia-ness must have rubbed off on me, because a very important box fell out of my coat when I was leaving the locker room earlier. Now most people would take that as a bad omen, but me? Me, I'm taking it as a sign that our life together will be filled with obstacles that we will overcome together. And although I don't have a ring, and this is not how I planned on asking this, Casey, will you marry me?"

"Der-ek!"

"Uhh… I'm gonna need a lil bit more than that… Yes? No? Maybe so? By the way, my knee is getting frostbite," Derek joked.

"Stand up! Oh my gosh… YES! Of course I'll marry you!"

Casey pulled Derek up and kissed him with all the passion she could as tears fell from her eyes. Unbeknownst to the couple, everyone else in the rink had stopped skating and began to clap bringing Derek and Casey out of their embrace.

"I'M GETTING MARRIED, TORONTO!"

As Derek leant in for another kiss, Casey skated backwards a bit reaching behind her neck to undo her necklace. Taking Derek's palm, Casey placed the chain in it and closed his fingers around it. "Ask me again."

Derek opened his hand to see a diamond ring, Nora's engagement ring.

"Casey?"

"Mom gave me this as a symbol of true love. She wears the new one George gave her when they renewed their vows, and gave this to me as a heirloom, I guess. I'd be honoured if my favourite Venturi placed it on my hand as hers did."

"Wow Case… ok."

Derek once again got down on his knee and reached for Casey's hand.

"Casey Ashley Macdonald. Will you do me the honour of spending the rest of your life by my side?"

"I most definitely will."

Derek placed the ring gingerly on Casey's finger before kissing her hand and pulling her into a bear hug.

"I love you, Space Case."

"I love you too. Dereka."

"HEY!"

**Hope you enjoyed. Please Review.**


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